Sodium Hydroxide → 4-[2-(3,4-Dichloro-phenoxy)-acetylamino]-thiophene-3-carboxylic acid

HRID 14603Notes

Reaction equation

HRID 14603 reaction equation
C[O:2][C:3]([C:5]1[C:9]([NH:10][C:11](=[O:22])[CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=2)=[CH:8][S:7][CH:6]=1)=[O:4].[OH-].[Na+]>C(O)C>[Cl:21][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][C:17]=1[Cl:20])[O:13][CH2:12][C:11]([NH:10][C:9]1[C:5]([C:3]([OH:4])=[O:2])=[CH:6][S:7][CH:8]=1)=[O:22]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 686874584-[2-(3,4-Dichloro-phenoxy)-acetylamino]-thiophene-3-carboxylic acid methyl ester

Product 1

HCID 160681574-[2-(3,4-Dichloro-phenoxy)-acetylamino]-thiophene-3-carboxylic acidYield 80.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 4-[2-(3,4-dichloro-phenoxy)-acetylamino]-thiophene-3-carboxylic acid methyl ester (80 mg, 0.222 mmol) in suspension in ethanol was added an aqueous solution of sodium hydroxide (1N, 0.333 mL, 0.333 mmol) and the reaction mixture was stirred at room temperature for 48 hours. After such time the reaction mixture was filtered and the filtrate was neutralized by addition of an aqueous solution of hydrochloric acid (1N, 0.335 mL). The precipitate was then isolated by filtration, washed with water and dried in vacuo to yield the title compound as a white solid (62.1 mg, 80%).

Workup

  1. filtrationAfter such time the reaction mixture was filtered
  2. additionthe filtrate was neutralized by addition of an aqueous solution of hydrochloric acid (1N, 0.335 mL)
  3. customThe precipitate was then isolated by filtration
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-1a0f7243e5134db39c034da113be3b4c
Source dataset
uspto-grants-2010_06
Patent number
US07732452B2

Reaction notes

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